HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (1s,2s)-2-Phenyl-cyclopropanecarboxylic acid (6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | trans-2-Phenylcyclopropanecarboxylic acid | HCID 237413 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 8-Amino-2-phenyl-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-one | HCID 135774079 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Diethylether ethylacetate | HCID 21584169 | — |
| Product | (1s,2s)-2-Phenyl-cyclopropanecarboxylic acid (6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-amide | HCID 136141668 | 14% |
Reaction Steps
Preparation of example 45 from the title compound of Example 7 (30 mg, 0.11 mmol), ±trans-2-phenyl-1-cyclopropanecarboxylic acid (26 mg, 0.16 mmol), triethylamine (0.076 mL, 0.55 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (62 mg, 0.16 mmol) in N,N-dimethylformamide (1.0 mL) was carried out analogously to Example 11. Silica gel chromatography (1:1 ethyl acetate:hexane), also in an analogous manner, followed by trituration with ethyl acetate/diethyl ether afforded the title compound (6.5 mg, 0.015 mmol) (mixture of trans diastereomers) as a yellow powder in 14% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07132533B2 |
| Source dataset | uspto-grants-2006_11 |
| ORD ID | ord-aafa03db135d4e7798a69e9d008c23fd |
| Source note | uspto-grants-2006_11 |